How to Overcome Challenges in Cold Calling for Tech Sales: A Top Seller’s Guide

I came from 10 years of copier sales. 20 cold calls a day. “Never take no.” I trained 70 reps on it as a leader at Ricoh.

My territory was Koreatown in LA. Every day I walked into 20–30 businesses, cold, with “no soliciting” signs. And I got thrown out, literally. over and over again.

But that year taught me grit. It taught me persistence.

I used to teach cold calling techniques. Tonality. Pacing. Objection handling. And while that still matters, it’s not the reason I consistently get meetings with C-level buyers.

The secret? I never cold call anymore. I warm call.

So how do you overcome the biggest cold calling challenges in tech sales? Stop cold calling people who’ve never heard of you. Start with a personalized, relevant email, then call their cell phone and reference it. Stack 8–12 touchpoints across email, phone, and LinkedIn. And work on yourself, because most salespeople don’t have sales problems. They have personal problems that show up in their sales.

I’ve coached 1,000+ reps and closed over $100M in enterprise software deals. Here’s how to overcome challenges in cold calling for tech sales.

The Biggest Cold Calling Challenges in Tech Sales at a Glance 

Here’s a quick look at the most common cold calling challenges tech sellers face, why they happen and how to overcome them, so you can jump straight to the section that matters most to you.

Cold calling challenge	Why it happens	How to overcome it
Fear of rejection	Calls feel disconnected from your bigger goals, so every “no” feels personal	Challenge the limiting belief and link each call to your life vision
Transactional pitching	Selling at department level puts executives on guard	Focus on fewer accounts and build deeper executive relationships
Calling the wrong people	Prospecting across the whole patch spreads effort thin	Target your top 10–20 A accounts at VP level and above
Prospects have never heard of you	Pure cold calls start with zero context	Send a personalised email first, then call their cell the same day
Weak call openers	Leading with a pitch triggers resistance	Reference your email and give a clear reason for calling
Low connect rates	iPhones filter unknown numbers	Call direct cell numbers and follow up with a text and voice memo
Giving up too early	Most reps stop after around 3 touches	Plan for 8–12 touches across email, phone and LinkedIn

1. Why is cold calling so hard in tech sales?

Cold calling is hard because it exposes the things you haven’t dealt with yet. Sales is a mirror to your soul, and the phone is where you see your reflection most clearly.

If you have a fear of rejection, cold calling will test it fast. Dial 100 strangers a week and you’ll hear “no” more often than most people hear it in a year. If you struggle with imposter syndrome, it shows up the moment you’re pitching a CIO who clearly knows more about their tech stack than you do. And if you tend to procrastinate, cold calling is the task you’ll find a reason to push back, even though the work you avoid directly affects your pipeline and your income.

That’s why so many sellers get stuck. They treat cold calling as a skills problem and look for better scripts or openers. But these usually aren’t sales issues. They’re mindset issues, and until you address them, no script will make the phone feel any lighter.

2. How do you get over the fear of rejection on cold calls?

Most tech sellers don’t have a motivation problem. They have a connection problem. They don’t connect today’s cold calls, follow-ups, and rejections to tomorrow’s vision for their life.

So they procrastinate. They avoid prospecting.

Start with the limiting belief: “I can’t succeed in sales because I’m not good at prospecting.”

What happens when you believe that thought? You don’t prospect, and you feel bad about yourself because of it. You waste time. Your pipeline is dry. Your results suffer.

Who would you be without that thought? Confident. Fearless. Actively prospecting. Focused on helping your customers.

Now turn it around: I CAN succeed in sales because I’m GREAT at prospecting.

3. Why doesn’t transactional cold calling work in enterprise tech sales?

At Salesforce, I showed up and threw up. Every meeting had one goal: find an opportunity and advance the deal.

That works in transactional sales. In enterprise, it makes people put their guard up. Nobody wants to be sold to.

My rock bottom was the year I sold more deals than anyone on my team and finished at 95%. The deals were small. I was selling at the department level.

The shift that made me #1? Doing less. Not more. Fewer accounts. Higher contacts. Deeper relationships.

I stopped spending a little time with a lot of people at the department level and started spending a lot of time with fewer people at the executive level. To take those executive relationships through to signature, read our latest blog, How to Close Enterprise Tech Sales.

4. Who should you actually be calling?

Go narrow before you go deep. Stop prospecting to everyone in your patch. Pick your A accounts, the top 10–20 that would change your year if you closed them.

Then go to the executives. They own business outcomes. Never take no from somebody who can’t say yes.

Once I made the decision to target VP levels and above with my prospecting, I discovered that deal cycles compressed compared to bottom-up selling. The quicker you get above the power line within an organization, the faster the sales cycle will be.

5. How do you turn a cold call into a warm call?

Most AEs fail on the phone for one simple reason: they’re cold calling people who’ve never heard of them.

Start with a personalized, relevant email. Do some quick research. Make it about them. You must “show me you know me!”

That matters. In a Gartner survey of 632 B2B buyers, 73% said they actively avoid suppliers who send irrelevant outreach.

That same day, a few hours later, call their cell phone. ZoomInfo or LinkedIn can get you that. No excuses.

DO NOT call the office. DO NOT waste time dialing assistants.

The call makes the email work. Across 300 million-plus cold calls analyzed by Gong, calling nearly doubled email reply rates (3.44% vs. 1.81%), even when the call didn’t connect.

Learn how to write emails that get read in our latest blog, A Guide to Write B2B Tech Sales Emails.

6. What should you say when an executive picks up?

When I call, I say: “Hi, this is Ian Koniak. Did you happen to see the email I sent this morning?”

If they say no: “No problem. I sent it because I saw your team’s quota attainment is down since 2022. I think I can help based on what I’ve done with other clients. Do you have a couple minutes now, or should we find time to connect on Zoom?”

It’s not a pitch. It’s a reference to something you already sent that’s about them. That’s what makes it warm.

The data backs it up. When Gong analyzed 90,380 cold calls, opening with a clear reason for the call raised the success rate 2.1x.

Be interested, not interesting. The harder you try to sell, the more you will repel.

7. What do you do when nobody picks up?

iPhones are routing unknown numbers somewhere else automatically.

So my team went to cell phones. Every unanswered call gets a voice note, not pre-recorded, not automated. Real context. Real person. Real response.

If they don’t pick up, leave a text message with a voice memo instead of a voicemail. This way you can see when it disappears and know they’ve heard it.

Gong found the average rep connects on 5.4% of dials, while top-quartile reps connect on 13.3%, and those top reps prioritize direct dials.

The rep who does the uncomfortable thing, finds the cell number, and leaves the voice note wins by default.

8. How many times should you follow up?

Most AEs stop prospecting after 3 touches, when it takes an average of 8 touches to book a meeting.

My largest deals took 10–15 touches before the first meeting.

The CIO at St. Joe’s Hospital ignored the first 11 of my emails. For email 12, I found a Stanford healthcare success story and shared it. That got three words back: “How much customization?”

That deal closed in under four months. 20,000 users. $3M.

I didn’t know what I was doing. I just didn’t quit.

Most reps fail not because they stop too late. But because they stop too soon.

For more, read How to Build an Effective Prospecting Sequence.

Sales Forces You to Grow Up

No dials = no meetings. No meetings = no pipeline. No pipeline = no commission.

Every time you skip your prospecting block, you’re giving money away. Make it sacred. Block it. Set it to busy.

Sales doesn’t just pay you to grow revenue. It forces you to grow up.

Knowing what to do is not enough. You must do it!

If you want tech sales coaching on the right structure, the right messaging, and the right mindset, check out Untap Your Sales Potential or book a free strategy call with my team.

Frequently Asked Questions

How do you overcome the biggest cold calling challenges in tech sales?

Warm call instead of cold calling. Research the account and send a personalized, relevant email first. Call the executive’s cell phone that same day and reference your message. If they don’t pick up, send a text with a voice memo. Follow up across email, phone, and LinkedIn until you break through, and work on the mindset that makes you avoid prospecting in the first place.

Is cold calling dead in tech sales?

Phone still works, if you use it right. In the crowded world of emails, cell phone still works best, and when it’s combined with a personalized text message and voice memo, it’s gold. Prospects don’t generally respond to automated email sequences, but they still respond to personalized, tailored phone calls and text messages.

What is the difference between a cold call and a warm call?

A cold call reaches someone who has never heard of you. A warm call comes right after you’ve sent a personalized email, so you open by asking whether they saw it and explain why you sent it. It’s not a pitch. It’s a reference to something you already sent that’s about them.

How many touchpoints does it take to book a meeting with an executive?

Expect around 10 high-quality touchpoints across three channels. A strong sequence is 6 emails, 3 phone calls, and 1 video spread over 20 days. Each message should educate the prospect rather than “bump” your last one. Most reps stop after two or three touches, which is exactly where the meetings are lost.

How do you stop procrastinating on cold calls?

Connect your prospecting to your life vision, then do the math. Work out your value per dial from your income planner and multiply it by your connects. When you see what a skipped calling block costs you, you’ll protect it. Block the time on your calendar, set it to busy, and treat it as sacred.